US4309425A - Miticidal, insecticidal, ovicidal and fungicidal N-(N',N'-diarylaminothio)sulfonamides - Google Patents

Miticidal, insecticidal, ovicidal and fungicidal N-(N',N'-diarylaminothio)sulfonamides Download PDF

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Publication number
US4309425A
US4309425A US06/134,883 US13488380A US4309425A US 4309425 A US4309425 A US 4309425A US 13488380 A US13488380 A US 13488380A US 4309425 A US4309425 A US 4309425A
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sub
phenyl
trifluoromethyl
dinitro
chloro
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Jiin-Duey Cheng
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EIDP Inc
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EI Du Pont de Nemours and Co
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Priority to US06/134,883 priority Critical patent/US4309425A/en
Priority to DK336780A priority patent/DK336780A/da
Priority to BR8005227A priority patent/BR8005227A/pt
Priority to AU61627/80A priority patent/AU6162780A/en
Priority to IL60900A priority patent/IL60900A0/xx
Priority to GR62726A priority patent/GR70077B/el
Priority to EP80302933A priority patent/EP0024906A1/en
Priority to PL22636380A priority patent/PL226363A1/xx
Priority to PT71729A priority patent/PT71729A/pt
Priority to FI802661A priority patent/FI802661A7/fi
Priority to GB8027395A priority patent/GB2058761A/en
Assigned to E.I. DU PONT DE NEMOURS AND COMPANY, WILMINGTON, DE A CORP. OF DE reassignment E.I. DU PONT DE NEMOURS AND COMPANY, WILMINGTON, DE A CORP. OF DE ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: CHENG, JIIN-DUEY
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/04—Sulfonic acids; Derivatives thereof
    • A01N41/06—Sulfonic acid amides
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/04—Sulfonic acids; Derivatives thereof
    • A01N41/08—Sulfonic acid halides; alpha-Hydroxy-sulfonic acids; Amino-sulfonic acids; Thiosulfonic acids; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/12—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom not containing sulfur-to-oxygen bonds, e.g. polysulfides
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
    • C07C381/06—Compounds containing sulfur atoms only bound to two nitrogen atoms
    • C07C381/08—Compounds containing sulfur atoms only bound to two nitrogen atoms having at least one of the nitrogen atoms acylated

Definitions

  • This invention relates to insecticidal, miticidal, fungicidal and ovicidal sulfonamides, agricultural compositions containing them and methods of using them.
  • X is halogen
  • n is zero or an integer from one to three;
  • n zero or one
  • p is zero, one or two;
  • q is zero, one or two
  • U.K. Pat. No. 1,455,207 is the compound 2,5'-bistrifluoromethyl-2'-chloro-4,6-dinitrodiphenylamine.
  • the compounds are taught to have insecticidal, acaricidal and fungicidal properties.
  • R 2 is H, halogen, CN, NO 2 and/or alkyl optionally substituted with halogen and/or haloalkoxy; or XR' and R 2 , when ortho to one another, may be linked so as to form (with the 2-adjacent C-atoms of the phenyl ring) an optionally substituted dioxanyl ring.
  • the application teaches that the disclosed compounds have insecticidal, acaricidal, nematocidal, insect growth retardant, fungicidal and bactericidal activity.
  • R 1 , R 3 and R 4 are independently H, F, Cl, Br, NO 2 , CF 3 , OCF 3 , OCF 2 CF 2 H or S(O) k R 9 ;
  • R 2 is H, F, Cl, Br, NO 2 , CF 3 or S(O) k R 9 ;
  • R 5 is H, Cl, F, Br or NO 2 ;
  • Z is --NR 6 SO 2 R 13 , ##STR4##
  • R 6 is C 1 -C 8 alkyl, C 3 -C 5 alkoxyalkyl, C 2 -C 4 chloroalkyl, ##STR5## or R 14 CHCOR 15 ;
  • R 7 is H, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, Cl, Br or F;
  • R 8 is H, C 1 -C 12 alkyl, C 1 -C 4 alkoxy, Cl, Br, F, CF 3 , NO 2 , R 11 S(O) k or CO 2 R 12 ;
  • R 9 is C 1 -C 2 alkyl or C 1 -C 2 alkyl substituted with 2 to 4 atoms or Cl and/or F;
  • R 10 is H, NO 2 or CF 3 ;
  • R 11 is C 1 -C 2 alkyl or C 2 -C 4 dialkylamino
  • R 12 is C 1 -C 4 alkyl
  • R 13 is ##STR6## naphthyl, NR 16 R 17 , CF 3 or C 1 -C 20 alkyl; R 14 is H or CH 3 ;
  • R 15 is C 1 -C 4 alkoxy or N(R 17 ) 2 ;
  • R 16 is C 1 -C 3 alkyl, OCH 3 or ##STR7##
  • R 17 is C 1 -C 3 alkyl;
  • R 18 is H, C 1 -C 8 alkyl, ##STR8## or NR 16 R 17 ;
  • A is --(CH 2 ) 3 --, --(CH 2 ) 4 --, --(CH 2 ) 5 --, --X(CH 2 ) 2 --, or --X(CH 2 ) 3 --, where X is O, S or NR 19 and where X is bonded to the carbonyl carbon of Z;
  • R 19 is C 1 -C 4 alkyl, or phenyl optionally substituted with 1 or 2 groups selected from F, Cl, Br, CH 3 or OCH 3 ;
  • R 20 is NO 2 or CF 3 ;
  • k 0, 1 or 2;
  • n 1 or 2;
  • R 1 , R 2 , R 3 , R 4 and R 5 are hydrogen
  • R 2 is H, F, Cl or Br
  • R 4 is F, Cl, Br, CF 3 , OCF 3 , OCF 2 CF 2 H or S(O) k CF 3 ;
  • R 6 is C 1 -C 4 alkyl
  • R 7 is H, C 1 -C 3 alkyl, C 1 -C 3 alkoxy or Cl;
  • R 8 is H, C 1 -C 3 alkyl or Cl
  • R 10 is NO 2 ;
  • R 13 is ##STR10## naphthyl, NR 16 R 17 or C 1 -C 3 alkyl, where R 16 and R 17 are independently C 1 -C 2 alkyl.
  • R 1 and R 4 are independently Cl, CF 3 , OCF 3 , OCF 2 CF 2 H or S(O) k CF 3 ;
  • R 3 is H or S(O) k CF 3 ;
  • R 2 and R 5 are H;
  • R 13 is ##STR11## 2-naphthyl, N(CH 3 ) 2 or CH 3 .
  • the compounds of this invention represented by Formula I, can be prepared by the reaction of an anion of the diphenylamine of Formula II with an equivalent or excess of the sulfenyl chloride, ClSZ, in a suitable solvent as illustrated by the following equation: ##STR12##
  • Aprotic solvents such as tetrahydrofuran (THF), dioxane, methylene chloride, chloroform and toluene are suitable for this reaction.
  • the reaction temperature can be within the range of about -20° C. to 80° C., preferably about -10° C. to 30° C.
  • the anions of Formula III can be generated by treating compounds of Formula II with an equivalent amount or slight excess of a metal hydride such as sodium hydride or an alkali hydroxide such as potassium hydroxide in a suitable solvent at about -5° C. to 40° C.
  • a metal hydride such as sodium hydride or an alkali hydroxide such as potassium hydroxide in a suitable solvent at about -5° C. to 40° C.
  • Compounds of Formula I can also be prepared by the reaction of diphenylamines of Formula II with a sulfenyl chloride in the presence of an organic tertiary amine acid acceptor such as triethylamine, pyridine and the dialkylanilines, or an inorganic base such as potassium carbonate.
  • an organic tertiary amine acid acceptor such as triethylamine, pyridine and the dialkylanilines
  • an inorganic base such as potassium carbonate.
  • Diphenylamines of Formula II can be obtained by the procedures taught in Belgian Pat. No. 826,376 and European Patent Application 156, the disclosures of which are herein incorporated by reference.
  • the N-chlorothiosulfonamides of the formula ClSZ can also be prepared by a suitable modification, obvious to one skilled in the art, of the procedure taught in British Pat. No. 1,403,170, herein incorporated by reference.
  • Example 1 The procedure described in Example 1 may be used to prepare the compounds in Tables 1 through 4.
  • Useful formulations of the compounds of Formula I can be prepared in conventional ways. They include dusts, granules, pellets, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates and the like. Many of these may be applied directly. Sprayable formulations can be extended in suitable media and used at spray volumes of from a few pints of several hundred gallons per acre. High strength compositions are primarily used as intermediates for further formulation.
  • the formulations broadly, contain about 1% to 99% by weight of active ingredient(s) and at least one of (a) about 0.1% to 20% surfactant(s) and (b) about 5% to 99% solid or liquid diluent(s). More specifically, they will contain these ingredients in the following approximate proportions:
  • Typical solid diluents are described in Watkins et al., "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books, Caldwell, N.J. The more absorptive diluents are preferred for wettable powders and the denser ones for dusts.
  • Typical liquid diluents and solvents are described in Marsden, “Solvents Guide”, 2nd Ed., Interscience, New York (1950). Solubility under 0.1% is preferred for suspension concentrates; solution concentrates are preferably stable against phase separation at 0° C.
  • compositions are well known. Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in a hammer or fluid energy mill. Suspensions are prepared by wet milling (see, for example, Littler, U.S. Pat. No. 3,060,084). Granules and pellets may be made by spraying the active material upon preformed granular carriers or by agglomeration techniques. See J. E. Browning, "Agglomeration”, Chemical Engineering, Dec. 4, 1967, pp. 147 ff. and “Perry's Chemical Engineer's Handbook", 4th Ed., McGraw-Hill, New York (1963), pp. 8-59 ff.
  • the ingredients are thoroughly blended.
  • the liquid surfactant is added by spraying upon the solid ingredients in the blender. After grinding in a hammer mill to produce particles essentially all below 100 microns, the material is reblended and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) and packaged.
  • the ingredients are thoroughly blended, passed through an air mill, to produce an average particle size under 15 microns, reblended, and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) before packaging.
  • the ingredients are blended and ground in a hammer mill to produce a high strength concentrate essentially all passing a U.S.S. No. 50 sieve (0.3 mm openings). This material may then be formulated in a variety of ways.
  • the ingredients are thoroughly blended and packaged for use.
  • the ingredients are ground together in a sand mill to produce particles essentially all under five microns in size.
  • the ingredients are combined and stirred to produce a solution which can be emulsified in water for application.
  • the compounds of this invention may be used in several ways. First, they may be used to control arthropod pests of plant and animal. These include mites, insects and ticks.
  • miticides they may be used to protect plants from damage caused by these pests. More specifically, fruits, field crops, vegetables and ornamentals can be protected.
  • mites When mites come into contact with the compounds of this invention, either in the form of direct sprays or by walking over surfaces which have been treated, they are killed if they have been exposed to a sufficiently high dosage. While most plants are able to tolerate the presence of very small numbers of mites without adverse effect, the reproductive capacity of these pests is enormous. Generally, mite populations rapidly build up, easily out-stripping parasite and predator capabilities for control. Growers noting rapid mite build-up must take immediate action to prevent damage to economically important crops. Thus, there is a need for immediately reducing mite build-up and thereby preventing damage to important crops.
  • the method of this invention namely, contacting mites with a miticidally effective concentration, is a most desirable method for control of these pests. This may be accomplished by applying an effective amount of a compound of this invention to the locus of infestation, to the area to be protected or to the pests themselves.
  • the quantity of compound needed for miticidal activity will vary depending on the specific situation; generally, a very small quantity is required.
  • the specific compound itself the specific mite to be controlled, weather conditions, the type of crop, the stage of development of the crop, the volume of spray applied, population pressure, and the interval between applications.
  • solutions or suspensions containing as little as 2.5 ppm of active ingredient in a spray solution may prove effective in a given set of circumstances.
  • 0.03 to 5.5 kilograms of active ingredient per hectare are acceptable, preferably 0.03 to 3 kilograms, and most preferably, 0.06 to 2 kg.
  • the compounds are especially suited for the protection of living plants such as fruit-bearing trees, nut-bearing trees, ornamental trees, forest trees, vegetable crops, horticultural crops (including ornamentals, small fruit and berries) and grain and seed crops.
  • Apple trees, peach trees, cotton, citrus trees, beans and peanuts are particularly susceptible to mite damage and can be protected by application of the compounds of this invention.
  • To assure control throughout the growing season e.g., June through August in the Northern Hemisphere
  • multiple applications at desired intervals can be utilized.
  • mites are controlled by the compounds of this invention.
  • the following is a list of representative susceptible mites along with the types of damage that they can cause: Panonychus ulmi (European red mite) and Tetranychus urticae (two-spotted mite) which are commonly called “orchard mites," and which attack a great many deciduous trees, such as apple, pear, cherry, plum and peach trees; Tetranychus atlanticus (Atlantic or strawberry mite), T. cinnabarinus (carmine spider mite) and T.
  • pacificus Pacific mite
  • Panonychus citri citrus red mite
  • Phyllocoptruta oleivora which causes citrus rust
  • Byrobia praetiosa clover mite which attacks clover, alfalfa and other crops
  • Eriophyes erinea which attacks grasses and other plants.
  • Test units consisted of plant pots containing two red kidney bean plants in the two-leaf stage per pot. The plants were infested with two-spotted mites and sprayed to run-off with solutions of N-butyl-N-[N-[2-chloro-5-(trifluoromethyl)phenyl]-N-[2,4-dinitro-6-(trifluoromethyl)phenyl]aminothio]-2-methylbenzenesulfonamide. Dispersions were made by dissolving weighed quantities of the active ingredients in 10 ml of acetone and then diluting to volume with water containing 1:3000 of a surfactant, Duponol® (a trade name of E. I. du Pont de Nemours and Co. for sodium alcohol sulfate). Mortality was evaluated two days after spraying.
  • a surfactant Duponol® (a trade name of E. I. du Pont de Nemours and Co. for sodium alcohol sulfate).
  • Test units consisted of plant pots containing two red kidney bean plants in the two-leaf stage per pot. The plants were infested with organo-phosphorous resistant two-spotted spider mites and sprayed to run-off with solutions of N-butyl-N-[N-[2-chloro-5-(trifluoromethyl)phenyl]-N-[2,4-dinitro-6-(trifluoromethyl)-phenyl]aminothio]-2-methylbenzenesulfonamide. Dispersions were made by dissolving weighed quantities of the active ingredient in 10 ml of acetone and then diluting to volume with water containing 1:3000 of a surfactant, Duponol®. Mite mortality was examined two days after spraying.
  • Test units consisted of plant pots containing two red kidney bean plants in the two-leaf stage per pot. The plants were infested with organo-phosphorous resistant two-spotted spider mites and sprayed to run-off with solutions of N-[N-[2-chloro-5-(trfluoromethyl)phenyl]-N-[2,4-dinitro-6-(trifluoromethyl)phenyl]-aminothio]-4-methyl-N-(1-methylethyl)benzenesulfonamide. Dispersions were made by dissolving weighed quantities of the active ingredient in 10 ml acetone and then diluting to volume with water containing 1:3000 of a surfactant, Duponol®. Mite mortality was evaluated two days after spraying.
  • Test units consisted of plant pots containing two red kidney bean plants in the two-leaf stage per pot. The plants were infested with organo-phosphorous resistant two-spotted spider mites and sprayed to run-off with solutions of N-[N-[2-chloro-5-(trifluoromethyl)phenyl]-N-[2,4-dinitro-6-(trifluoromethyl)phenyl]aminothio]-N,4-dimethylbenzenesulfonamide. Dispersions were made by dissolving weighed quantities of the active ingredient in 10 ml of acetone and then diluting to volume with water containing 1:3000 of a surfactant, Duponol®. Mite mortality was evaluated two days after spraying.
  • the compounds of this invention are useful for the control of insects. Both the eggs and the motile forms are susceptible.
  • the insects or insect eggs are controlled by applying the material in a convenient formulation to the locus of infestation, to the area to be protected, or to the pests themselves.
  • the compound is generally applied to the foliage or other plant parts which are to be protected. Effective amounts to be applied depend on the species to be controlled, its life stage, its size and location and other variables. In general, 0.1 to 10 kg/ha may be required for insect control in agriculture with rates of 0.25 to 4 kg/ha usually being sufficient. Preferred rates in large scale operations are in the range of 0.3 to 2 kg/ha.
  • insects species that may be controlled by ovicidal action of the compounds of this invention include, but are not limited to, Spodoptera exigua (beet armyworm), Spodoptera frugiperda (southern armyworm), Phthorimaea operculella (potato tuberworm), Heliothis zea (cotton bollworm) and Heliothis viresceus (tobacco budworm). These compounds are especially useful for controlling mosquito larvae.
  • Motile stages of insects include, but are not limited to, Anthonomus grandis (cotton boll weevil), Aphis fabae (bean aphid), Myzus persicae (green peach aphid), Epilachna varusestis (Mexican bean beetle) Melanoplus femurrubrum (redlegged grasshopper), and Camponotus pennsylvanicus (black carpenter ant).
  • compounds of this invention are generally applied to the locus of infestation, to the area to be protected or to the pests themselves. Effective compounds to be applied depend on the specific compound used, the species to be controlled, its life cycle, its size and location, the amount of rainfall, the time of year, moisture, temperature, type of application and other variables. In general, 0.001% to 10% solutions, dispersions, dusts, etc. may be required for anthropod control in these areas, with rates of 0.05% to 5% solution usually being sufficient in many situations. In efficient large scale operations, rates in the range of 0.01% to 2.5% solution are generally used.
  • the compounds of this invention are also useful as plant disease control agents. They are effective for the control of a broad spectrum of plant diseases as represented by, but not limited to, soil-borne fungal pathogens Rhizoctonia solani and Pythuim sp., foliar pathogens, Puccinia graminis, Erisyphe cichoracearum, Venturia inaequalis and Phytophthora infestans, fruit and vegetable rotting fungi, Sclerotinia sclerotiorum and Rhizopus stolonifer and the seedborne fungus Helminthosporium oryzae. Diseases of a wide variety of ornamental, vegetable, cereal and fruit crops are controlled by the compounds of this invention.
  • Disease control is accomplished by applying the compound to the portion of the plant to be protected, such as the roots, stems, foliage, fruit, seeds, tubers or bulbs, or to the media (soil or sand) in which the plants to be protected are growing.
  • the compound may also be applied to the seed from which the plants to be protected are to be grown.
  • Rates of application for these compounds will be influenced by many factors of the environment and must be determined under use conditions. Foliage can normally be protected when treated at a rate of from 1 to 500 ppm of active ingredient. Plants growing in soil treated at a concentration of from 0.1 to about 20 kg/ha can be protected from disease. Seed and seedlings can normally be protected when seed is treated at a rate of from 0.06 to about 3 grams per kilogram of seed.
  • Rice seed infected with Helminthosporium oryzae are treated with compounds of this invention at a rate of 1.3 g per kilogram of seed. This is accomplished by soaking infected seed for 1 minute in a suspension of the indicated compound dissolved in a solution containing 4% glycerine, 4% water, 0.02% Tween®20, and 92% acetone. Treated seed are placed on moist blotters and enclosed in plastic bags for 18 days at which time disease ratings are made based on percent germination. As shown in the following table, compounds of this invention provided excellent disease control, as treated seed had a high percentage germination in contrast to untreated seed which did not germinate. Phytotoxicity in the form of growth reduction was observed on germinated seedlings in association with disease control.
  • Pythium infested soil was placed in a 900 cc cup.
  • Compounds of this invention were mixed at a rate of 1.5 kg/ha in a section 2" wide ⁇ 2" deep ⁇ 4" long to simulate an in-the-row application.
  • Five cotton seeds were planted in the treated soil. After 8 days, the cotton plants were removed and rated for disease control. Phytotoxicity in the form of growth reduction was observed on some of the plants in association with disease control.
  • Rhizoctonia solani-infested soil was placed in a 900 cc cup. Compounds of this invention were mixed at a rate of 1.5 kg/ha in a section 2" wide ⁇ 2" deep ⁇ 4" long to simulate an in-the-row application. Five cotton seeds were planted in the treated soil. After 8 days, the cotton plants were removed and rated for disease control. Phytotoxicity in the form of growth reduction was observed on some of the plants in association with disease control.
  • Compounds of this invention are dissolved in acetone in an amount equal to 6% of the final volume and then suspended at a concentration of 20 ppm in purified water containing 25 ppm of the surfactant Alkanol® XC (sodium alkyl naphthalene sulfonate). This suspension is sprayed to the point of run-off on apple seedlings. The following day, the plants are inoculated with a spore suspension of the fungus Venturia inaequalis and incubated in a growth room for 10-12 days. Disease ratings are then made.
  • Compounds of this invention are dissolved in acetone in an amount equal to 6% of the final volume and then suspended at a concentration of 20 ppm in purified water containing 25 ppm of the surfactant Alkanol® XC (sodium alkyl naphthalene sulfonate). This suspension is sprayed to the point of run-off on apple seedlings. The following day, 1/2 inch of simulated rainfall is applied to the foliage of the plants. When the foliage is dry, the plants are inoculated with a spore suspension of the fungus Venturia inaequalis and incubated in a growth room for 10-12 days. Disease ratings are then made.
  • Alkanol® XC sodium alkyl naphthalene sulfonate
  • Compounds of this invention are dissolved in acetone in an amount equal to 6% of the final volume and then suspended at a concentration of 20 ppm in purified water containing 25 ppm of the surfactant Alkanol® XC (sodium alkyl naphthalene sulfonate). This suspension is sprayed to the point of run-off on apple seedlings. When the foliage is dry, the plants are exposed to 3500 foot candles of light from a xenon arc source for a period of 16 hours. This light source approximates the spectrum of natural sunlight, and is used to assess photostability of the compounds of this invention on plant foliage.
  • Alkanol® XC sodium alkyl naphthalene sulfonate
  • the plants are inoculated with a spore suspension of the fungus Venturia inaequalis and incubated in a growth room for 10-12 days. Disease ratings are then made. As shown in the following table, most of the compounds of this invention provided excellent disease control, as some of the treated plants had little or no apple scab lesions in contrast to untreated plants which were covered with scab lesions. Phytotoxicity in the form of foliar burn was observed on some of the plants in association with disease control.
  • Compounds of this invention are dissolved in acetone in an amount equal to 6% of the final volume and then suspended at a concentration of 20 ppm in purified water containing 25 ppm of the surfactant Alkanol® XC (sodium alkyl naphthalene sulfonate). This suspension is sprayed to the point of run-off on cucumber seedlings. The following day, the plants are inoculated with a spore suspension of the fungus Erysiphe cichoracearum and incubated in a growth room for 7 days. Disease ratings are then made.
  • Cucumber plants are inoculated with a spore suspension of the fungus Erisyphe cichoracearum and in a growth room overnight. The following day, the plants are sprayed to the point of run-off with a suspension prepared by dissolving compounds of this invention in acetone in an amount equal to 6% of the final volume and then suspended at a concentration of 20 ppm in purified water containing 25 ppm of the surfactant Alkanol® XC (sodium alkyl naphthalene sulfonate). Plants are returned to the growth room for an additional 6 days when disease ratings are then made.
  • Compounds of this invention are dissolved in acetone in an amount equal to 6% of the final volume and then suspended at a concentration of 20 ppm in purified water containing 25 ppm of the surfactant Alkanol® XC (sodium alkyl naphthalene sulfonate). This suspension is sprayed to the point of run-off on cucumber seedlings. The following day, 1/2 inch of simulated rainfall is applied to the foliage of the plants. When the foliage is dry, the plants are inoculated with a spore suspension on the fungus Erysiphe cichoracearum and incubated in a growth room for 7 days. Disease ratings are then made. As shown in the following table, most of the compounds of this invention provided excellent disease control, as treated plants had little or no powdery mildew in contrast to untreated plants where were covered with powdery mildew.
  • Alkanol® XC sodium alkyl naphthalene sulfonate
  • Compounds of this invention are dissolved in acetone in an amount equal to 6% of the final volume and then suspended at a concentration of 20 ppm in purified water containing 25 ppm of the surfactant Alkanol® XC (sodium alkyl naphthalene sulfonate). This suspension is sprayed to the point of run-off in cucumber seedlings. When the foliage is dry, the plants are exposed to 3500 foot candles of light from a xenon arc source for a period of 16 hours. This light source approximates the spectrum of natural sunlight, and is used to assess photostability of the compounds of this invention on plant foliage.
  • Alkanol® XC sodium alkyl naphthalene sulfonate
  • Compounds of this invention are dissolved in acetone in an amount equal to 6% of the final volume and then suspended at a concentration of 20 ppm in purified water containing 25 ppm of the surfactant Alkanol® XC (sodium alkyl naphthalene sulfonate). This suspension is sprayed to the point of run-off on tomato seedlings. The following day, the plants are inoculated with a spore suspension of the fungus Phytophthora infestans and incubated in a growth room for 4 days. Disease ratings are then made. As shown in the following table, several of the compounds of this invention provided excellent disease control, as treated plants had no late blight lesions in contrast to untreated plants which were covered with lesions. Phytotoxicity in the form of foliar burn was observed on some of the plants in association with disease control.
  • Compounds of this invention are dissolved in acetone in an amount equal to 6% of the final volume and then suspended at a concentration of 20 ppm in purified water containing 25 ppm of the surfactant Alkanol® XC (sodium alkyl naphthalene sulfonate). This suspension is sprayed to the point of run-off on tomato seedlings. The following day, 1/2 inch of simulated rainfall is applied to the foliage of the plants. When the foliage is dry, the plants are inoculated with a spore suspension of the fungus Phytophthora infestans and incubated in a growth room for 4 days. Disease ratings are then made.
  • Alkanol® XC sodium alkyl naphthalene sulfonate
  • Compounds of this invention are dissolved in acetone in an amount equal to 6% of the final volume and then suspended at a concentration of 20 ppm in purified water containing 25 ppm of the surfactant Alkanol® XC (sodium alkyl naphthalene sulfonate). This suspension is sprayed to the point of run-off on tomato seedlings. When the foliage is dry, the plants are exposed to 3500 foot candles of light from a xenon arc source for a period of 16 hours. This light source approximates the spectrum of natural sunlight, and is used to assess photostability of the compounds of this invention on plant foliage.
  • Alkanol® XC sodium alkyl naphthalene sulfonate
  • the plants are inoculated with a spore suspension of the fungus Phytophthora infestans and incubated in a growth room for 4 days. Disease ratings are then made. As shown in the following table, most of the compounds of this invention provided excellent disease control, as treated plants had little or no late blight lesions in contrast to untreated plants which were covered with lesions. Phytotoxicity in the form of foliar burn was observed on some of the plants in association with disease control.
  • the untreated cups were completely covered with Rhizopus mycelial growth, but the treated cups were mostly free of growth by this disease-causing organism.
  • the miticidal, insecticidal, ovicidal and fungicidal compositions of this invention may contain, in addition to a compound of this invention, other agricultural pesticides or adjuvants.
  • Pesticides with which the compounds of this invention may be mixed to achieve broader-spectrum activity include:
  • thiuram tetramethyl thiuram disulfide

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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US06/134,883 1979-08-24 1980-04-11 Miticidal, insecticidal, ovicidal and fungicidal N-(N',N'-diarylaminothio)sulfonamides Expired - Lifetime US4309425A (en)

Priority Applications (11)

Application Number Priority Date Filing Date Title
US06/134,883 US4309425A (en) 1979-08-24 1980-04-11 Miticidal, insecticidal, ovicidal and fungicidal N-(N',N'-diarylaminothio)sulfonamides
DK336780A DK336780A (da) 1979-08-24 1980-08-05 Miticide insecticide ovicide og fungicide n-(n!,n!-diarylaminothio) sulfonamider
BR8005227A BR8005227A (pt) 1979-08-24 1980-08-19 Composto agricola; composicao e processo para o controle de acaros, insetos ou ovos de insetos, doencas de fungos de uma planta e processo para a preparacao de um composto agricola
AU61627/80A AU6162780A (en) 1979-08-24 1980-08-21 Miticidal, insecticidal, ovicidal and fungicidal n-(n'- diarylaminothio) sulfonamides
GR62726A GR70077B (en:Method) 1979-08-24 1980-08-22
EP80302933A EP0024906A1 (en) 1979-08-24 1980-08-22 Miticidal, insecticidal, ovicidal and fungicidal diarylaminothio derivatives, and preparation, compositions and use thereof
IL60900A IL60900A0 (en) 1979-08-24 1980-08-22 N-(n',n',-diarylaminothio)sulfonamides,their preparation and pesticidal compositions containing them
PL22636380A PL226363A1 (en:Method) 1979-08-24 1980-08-22
PT71729A PT71729A (en) 1979-08-24 1980-08-22 Process for preparing miticidal insecticidal ovicidal and fungicidal n-(n',n'-diarylaminothio) sulfonamides
FI802661A FI802661A7 (fi) 1979-08-24 1980-08-22 Punkkeja, hyönteisiä, niiden munia ja sieniä tuhoavia N-(N'- diaryyliaminotio)sulfonamideja.
GB8027395A GB2058761A (en) 1979-08-24 1980-08-22 Miticidal insectidal ovicidal and fungicidal diaryaminothio derivatives and preparation compositions and use thereof

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US6975279A 1979-08-24 1979-08-24
US06/134,883 US4309425A (en) 1979-08-24 1980-04-11 Miticidal, insecticidal, ovicidal and fungicidal N-(N',N'-diarylaminothio)sulfonamides

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EP (1) EP0024906A1 (en:Method)
AU (1) AU6162780A (en:Method)
BR (1) BR8005227A (en:Method)
DK (1) DK336780A (en:Method)
FI (1) FI802661A7 (en:Method)
GB (1) GB2058761A (en:Method)
GR (1) GR70077B (en:Method)
IL (1) IL60900A0 (en:Method)
PL (1) PL226363A1 (en:Method)
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060073995A1 (en) * 2004-10-06 2006-04-06 Schneider David J Animal shampoo

Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1942790A (en) * 1931-03-12 1934-01-09 Ig Farbenindustrie Ag Vulcanization accelerator
US3107229A (en) * 1958-08-07 1963-10-15 Bayer Ag Process for stabilizing polyolefins
US3718738A (en) * 1969-01-30 1973-02-27 Chevron Res N-phenyl sulfenamides and their use as fungicides and onicides
DE2363602A1 (de) 1972-12-20 1974-06-27 Ici Ltd Nitrobenzolderivate
DE2509416A1 (de) 1974-03-07 1975-09-25 Ici Ltd Dinitrobenzotrifluoride
US3969350A (en) * 1972-03-15 1976-07-13 Monsanto Company Base catalysis of azolesulfenamides and sulfur to aminodithioazoles
GB1455207A (en) 1974-11-06 1976-11-10 Ici Ltd Substituted dinitro-diphenylamines and their pesticidal compositions
US4098900A (en) * 1975-03-10 1978-07-04 Ciba-Geigy Corporation N,N'-Diphenyl-guanidine derivatives
US4152460A (en) * 1978-01-30 1979-05-01 Eli Lilly And Company 3-Chloro-2,6-dinitro-N-(substituted phenyl)-4-(trifluoromethyl)benzenamines
US4182873A (en) * 1972-10-04 1980-01-08 Rhone-Poulenc S.A. Process for the preparation of thiazolesulphenamides
US4246283A (en) * 1976-06-04 1981-01-20 Ciba-Geigy Corporation Pesticidally active 1-phenyl-1,3,5-triaza-4-sulfa-5-alkylsulfonyl and -phenylsulfonyl-pent-1-en derivatives

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1355802A (en) * 1970-08-12 1974-06-05 Ici Ltd Amido or imido sulphenamides

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1942790A (en) * 1931-03-12 1934-01-09 Ig Farbenindustrie Ag Vulcanization accelerator
US3107229A (en) * 1958-08-07 1963-10-15 Bayer Ag Process for stabilizing polyolefins
US3718738A (en) * 1969-01-30 1973-02-27 Chevron Res N-phenyl sulfenamides and their use as fungicides and onicides
US3969350A (en) * 1972-03-15 1976-07-13 Monsanto Company Base catalysis of azolesulfenamides and sulfur to aminodithioazoles
US4182873A (en) * 1972-10-04 1980-01-08 Rhone-Poulenc S.A. Process for the preparation of thiazolesulphenamides
DE2363602A1 (de) 1972-12-20 1974-06-27 Ici Ltd Nitrobenzolderivate
DE2509416A1 (de) 1974-03-07 1975-09-25 Ici Ltd Dinitrobenzotrifluoride
GB1455207A (en) 1974-11-06 1976-11-10 Ici Ltd Substituted dinitro-diphenylamines and their pesticidal compositions
US4098900A (en) * 1975-03-10 1978-07-04 Ciba-Geigy Corporation N,N'-Diphenyl-guanidine derivatives
US4246283A (en) * 1976-06-04 1981-01-20 Ciba-Geigy Corporation Pesticidally active 1-phenyl-1,3,5-triaza-4-sulfa-5-alkylsulfonyl and -phenylsulfonyl-pent-1-en derivatives
US4152460A (en) * 1978-01-30 1979-05-01 Eli Lilly And Company 3-Chloro-2,6-dinitro-N-(substituted phenyl)-4-(trifluoromethyl)benzenamines

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Biba et al., Chem. Abst., 74, (1971), #141169b.

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060073995A1 (en) * 2004-10-06 2006-04-06 Schneider David J Animal shampoo
US7384899B2 (en) * 2004-10-06 2008-06-10 Schneider Advanced Technologies, Inc. Animal shampoo

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EP0024906A1 (en) 1981-03-11
FI802661A7 (fi) 1981-01-01
PL226363A1 (en:Method) 1981-06-05
BR8005227A (pt) 1981-03-04
IL60900A0 (en) 1980-10-26
PT71729A (en) 1980-09-01
DK336780A (da) 1981-02-25
GR70077B (en:Method) 1982-07-27
AU6162780A (en) 1981-04-09
GB2058761A (en) 1981-04-15

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